Details of Grant 

EPSRC Reference:	GR/J23501/01
Title:	CHIRAL (2.2)PARACYCLOPHANE DERIVATIVES AS PLANAR CHIRAL COMPOUNDS IN ASYMMETRIC SYNTHESIS
Principal Investigator:	Pelter, Professor A
Other Investigators:	Smith, Professor K
Researcher Co-Investigators:
Project Partners:
Department:	Chemistry
Organisation:	Swansea University
Scheme:	Standard Research (Pre-FEC)
Starts:	01 November 1993	Ends:	31 October 1996	Value (£):	120,929
EPSRC Research Topic Classifications:	Asymmetric Chemistry
EPSRC Industrial Sector Classifications:
Related Grants:
Panel History:
Summary on Grant Application Form
Planar chiral [2.2] paracyclophane ([2.2]PC) derivatives will be used as Ar*X to open up a new field of synthetic chiral reactions and reagents. The thermal and conformational stability of such homochiral compounds makes them ideal reagent with predictable reactivity. The intrinsic differential shielding of the two sides of each aromatic ring can be tuned by -geminal substitution, so that inert hydrocarbon groups on one ring are close to, and parallel with, functional groups on the other ring. Thus reagents or substrates can be forced to approach from one plane only. The chemistry of [2.2]PC's is well developed and homochiral derivatives have been characterised. However, astonishingly, only two examples are know to us, or chiral reactions using [2.2]PC derivatives. We shall make homochiral Ar* and the chirally stable Ar*MetX. From these we shall make and study a series of stable chiral derivatives. (a) Ar*BH2, Ar*2BH, Ar*BAllyl, Ar*BHR2, Ar*2BHR. These will be studies for chiral reductions, hydroborations and allylations. (b) Ar*OH and Ar*OH and Ar*NHSO2Ph will be studied as chiral auxiliaries. The derived esters (and amides) will be metallated and alkylations and aldol reactions studied. Michael reactions of derived unsaturated esters and amides will be surveyed (c) the ortho-quinols Ar*(OH)2 will be studied as catalysts for NaBH4 reactions, and the derived boranes will be examined as direct chiral replacements for catecholborane in reductions and chiral allylations.
Key Findings
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
Potential use in non-academic contexts
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
Impacts
Description This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk Summary Date Materialised
Sectors submitted by the Researcher
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
Project URL:
Further Information:
Organisation Website:	http://www.swan.ac.uk